ACCEPTED MANUSCRIPT
26.8, 22.1, 20.6, 16.4, 12.2. IR (KBr ν (cm-1)) 3127(NH), 1690 (CON); MS m/z (rel int.): 367 (100, (M-1)-);
MS2 (367) m/z (rel int.): 367 (100, (M-1)-), 323 (73), 307 (77), 283 (43).
3-Methoxy-N-(4H-1,2,4-triazol-4-yl)estra-16-ene-17-carboxamide (4a). Yield: 252.4 mg (67%), white
solid, mp 269–270 °C; [Found: C, 69.66; H, 6.81; N, 14.56%, C22H26N4O2 requires C, 69.82; H, 6.92; N,
14.80%]; δH (500 MHz, DMSO) 11.48 (1H, s, NH), 8.70 (2H, s, CH(triazole)), 7.16 (1H, d, J = 8.5 Hz, 1-CH),
6.78 (1H, br s, =CH), 6.69 (1H, dd, J = 8.7, 2.6 Hz, 2-CH), 6.63 (1H, d, J = 2.4 Hz, 4-CH), 3.70 (3H, s,
OCH3), 2.82-2.85 (2H, m, 6-CH2), 2.41 (1H, ddd, J = 16.8, 6.3, 3.2 Hz, 15-CHeqHax), 2.16–2.27 (4H, m, 9-CH,
10- and 11-CHeqHax, 15-CHaxHeq), 1.87-1.90 (1H, m, 7-CHeqHax), 1.37–1.66 (5H, m, 8- and 14-CH, 7-,10- and
11-CHaxHeq), 0.95 (3H, s, 18-CH3); δC (125.7 MHz, DMSO) 164.2, 157.6, 146.8, 144.4, 139.8, 137.8, 132.6,
126.3, 114.0, 111.9, 55.6, 55.4, 47.3, 44.2, 37.1, 34.7, 32.1, 29.5, 27.7, 26.5, 16.7. IR (KBr ν (cm-1)): 3124
(NH), 1679 (CON); MS m/z (rel int.): 377 (100, (M-1)-); MS2 (377) m/z (rel int.): 377 (17, (M-1)-), 364 (37),
337 (30), 311 (100), 255 (23), 183 (11), 125 (12).
N-(4H-1,2,4-Triazol-4-yl)benzamide (5a). Yield: 178.4 mg (95%), white solid, mp 242–243 °C; [Found:
C, 57.20; H, 4.41; N, 29.65%, C9H8N4O requires C, 57.44; H, 4.28; N, 29.77%]; δH (500 MHz, DMSO) 12.12
(1H, br s, NH), 8.79 (2H, s, CH(triazole)), 7.96 (2H, d, J = 7.0 Hz, Hortho(Ph)), 7.69 (1H, t, J = 7.3 Hz,
Hpara(Ph)), 7.60 (2H, t, J = 7.6 Hz, Hmeta(Ph)); δC (125.7 MHz, DMSO) 166.2, 144.3, 133.4, 131.3, 129.3,
128.2. IR (KBr ν (cm-1)) 3108 (NH), 1676 (CON); MS m/z (rel int.): 187 (100, (M-1)-); MS2 (187) m/z (rel
int.): 187 (11, (M-1)-), 68 (100).
4-(tert-Butyl)-N-(4H-1,2,4-triazol-4-yl)benzamide (6a). Yield: 236.5 mg (97%), palebrown needle
crystal, mp. 214-215 °C; [Found: C, 56.11; H, 6.44; N, 29.01%, C13H16N4O requires C, 63.92; H, 6.60; N,
22.93%]; δH (500 MHz, DMSO) 12.02 (1H, br s, NH), 8.77 (2H, s, CH(triazole)), 7.90 (2H, d, J = 8.5 Hz,
CH(Ph)), 7.61 (2H, d, J = 8.5 Hz, CH(Ph)), 1.33 (9H, s, CH3); δC (125.7 MHz, DMSO) 166.1, 156.4, 144.3,
128.5, 128.1, 126.1, 35.3, 31.3. IR (KBr ν (cm-1)) 3118 (NH), 1677 (CON); MS m/z (rel int.): 243 (100, (M-1)-
); MS2 (243) m/z (rel int.): 243 (100, (M-1)-), 216 (31), 109 (28), 68 (43).
4-Methyl-N-(4H-1,2,4-triazol-4-yl)benzamide (7a). Yield: 188.6 mg (93%), pale brown crystal, mp 219–
220 °C; [Found: C, 59.34; H, 5.04; N, 27.56%, C10H10N4O requires C, 59.40; H, 4.98; N, 27.71%]; δH (500
MHz, DMSO) 12.02 (1H, s, NH), 8.78 (2H, s, CH(triazole)), 7.86 (2H, d, J = 7.9 Hz, CH(Ph)), 7.40 (2H, d, J
= 7.9 Hz, CH(Ph)), 2.41 (3H, s, CH3); δC (125.7 MHz, DMSO): 166.1, 144.3, 143.6, 129.8, 128.5, 128.2, 21.6.
IR (KBr ν (cm-1)) 3110 (NH), 1678 (CON); MS m/z (rel int.): 201 (100, (M-1)-); MS2 (201) m/z (rel int.): 201
(100, (M-1)-), 68 (25).
12